Exam 14: Aromatic Compounds

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In the 1H NMR spectra of which of the following substances,C9H10O,would you expect to see two singlets in the range of δ\delta 2.0-2.5 ppm?  In the <sup>1</sup>H NMR spectra of which of the following substances,C<sub>9</sub>H<sub>10</sub>O,would you expect to see two singlets in the range of  \delta  2.0-2.5 ppm?

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How many resonances would be expected in the broadband proton-decoupled 13C spectrum of: How many resonances would be expected in the broadband proton-decoupled <sup>13</sup>C spectrum of:

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Aniline is the name commonly assigned to:

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Briefly explain why the aromatic hydrocarbon azulene,C10H8,possesses a significant dipole moment.Use diagrams as needed to illustrate/clarify your answer.

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Which dibromobenzene can yield only one mononitro derivative?

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Which of the following substances,C9H10O,would exhibit seven signals in its 13C NMR spectrum? Which of the following substances,C<sub>9</sub>H<sub>10</sub>O,would exhibit seven signals in its <sup>13</sup>C NMR spectrum?

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Consider the oxygen atom in the molecules of furan and tetrahydrofuran.Bearing in mind that furan exhibits aromatic properties,compare the hybridization of oxygen in both species,explaining why it must be different,although at first glance,it may appear identical. Consider the oxygen atom in the molecules of furan and tetrahydrofuran.Bearing in mind that furan exhibits aromatic properties,compare the hybridization of oxygen in both species,explaining why it must be different,although at first glance,it may appear identical.

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Which cyclization(s)should occur with a decrease in pi-electron energy? Which cyclization(s)should occur with a decrease in pi-electron energy?

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On the basis of molecular orbital theory and Hückel's rule,which molecules and/or ions should be antiaromatic? On the basis of molecular orbital theory and Hückel's rule,which molecules and/or ions should be antiaromatic?

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Application of the polygon-and-circle technique reveals that single electrons occupy each of the two nonbonding orbitals in the molecular orbital diagram of:

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The pKa of cyclopentadiene is found to be 16 while,by contrast,that of cycloheptatriene is found to be 36.Explain the large difference found in the two pKa values.

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For which of the following substances,C9H10O,would the aromatic multiplet,in its 1H NMR spectrum,consist of two doublets? For which of the following substances,C<sub>9</sub>H<sub>10</sub>O,would the aromatic multiplet,in its <sup>1</sup>H NMR spectrum,consist of two doublets?

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4-Amino-2-chlorophenol is: 4-Amino-2-chlorophenol is:

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Of the following C-10 compounds,which is expected to possess the greatest resonance (delocalization)energy? Of the following C-10 compounds,which is expected to possess the greatest resonance (delocalization)energy?

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Cumene is the name commonly assigned to:

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Which of these compounds absorbs at the longest wavelength in the UV-visible region? Which of these compounds absorbs at the longest wavelength in the UV-visible region?

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Predict the product of the reaction of one equivalent of hydrochloric acid with the organic compound shown: Predict the product of the reaction of one equivalent of hydrochloric acid with the organic compound shown:

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Pyrrole is not particularly basic,because the lone pair on the nitrogen is ___.

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Of Hückel's requirements for aromatic character,only this one is waived in the case of certain compounds considered to be aromatic.

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Which compound would you NOT expect to be aromatic? Which compound would you NOT expect to be aromatic?    Which compound would you NOT expect to be aromatic?

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